Acetic Acid → HCID 67922678, compound

HRID 704214Notes

Reaction equation

HRID 704214 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH:9]([N:11]1[C:24]2[CH:23]=[C:22]([C:25](=S)[NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:21]=[CH:20][C:19]=2[S:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10].C(O)(=[O:35])C>>[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH:9]([N:11]1[C:24]2[CH:23]=[C:22]([C:25]([NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:35])[CH:21]=[CH:20][C:19]=2[S:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10]

Participants

3

Reactant 2

HCID 176Acetic Acid2×HCID 54252607HCID 54252607, compound

Product 1

HCID 67922678HCID 67922678, compound

Conditions

Temperature
20 °C

Procedure

Mercuric acetate (2.91 g) dissolved in glacial acetic acid (60 cc) is added in the course of 20 minutes to a solution of 10-{1-[(2R)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-N-(3-methylbutyl)-2-phenothiazinecarbothioamide, L series (4.29 g) in acetic acid (60 cc), and the mixture is stirred for 45 minutes at a temperature in the region of 20° C. The black suspension obtained is filtered on sintered glass plugged with celite and the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with ethyl acetate (250 cc) and distilled water (50 cc). The organic phase is washed successively with normal sodium hydroxide (2×100 cc) and distilled water (3×100 cc) and with saturated aqueous sodium chloride (100 cc) and dried over magnesium sulphate. After filtration, the yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and a crude yellow oil (4.6 g) is thereby obtained. This residue is purified by chromatography on a column (height: 25 cm; diameter: 3.0 cm) of silica gel (0.04-0.06 mm), eluting with pure ethyl acetate (3.6 liters) with a slight excess pressure of nitrogen (40 kPa) and collecting 150-cc fractions. Fractions 12 to 24 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-{1-[(2R)-2-h-ydroxymethyl-1-pyrrolidinyl]-2-propyl}-N-(3-methylbutyl)-2-phenothiazinecarboxamide, L series (0.89 g) in the form of an off-white solid, m.p. 140° C.

Workup

  1. customThe black suspension obtained
  2. filtrationis filtered on sintered glass
  3. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. distillationdistilled water (50 cc)
  5. washThe organic phase is washed successively with normal sodium hydroxide (2×100 cc)
  6. distillationdistilled water (3×100 cc)
  7. dry with materialwith saturated aqueous sodium chloride (100 cc) and dried over magnesium sulphate
  8. filtrationAfter filtration
  9. concentrationthe yellow filtrate is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  10. customa crude yellow oil (4.6 g) is thereby obtained
  11. customThis residue is purified by chromatography on a column (height: 25 cm; diameter: 3.0 cm) of silica gel (0.04-0.06 mm)
  12. washeluting with pure ethyl acetate (3.6 liters) with a slight excess pressure of nitrogen (40 kPa)
  13. customcollecting 150-cc fractions
  14. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-d4ef5c16e37540ff84e07968aeb82212
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…